[GSK]

Anyone have any tips for a succesful Wittig reaction? I have an 11-carbon Wittig salt, non-stabilized (bromide counterion), terminating in a methyl ester. It resists dissolving in THF, and when I add the base (NaHMDS), it partially solubilizes but it never goes all the way. When I go ahead and add the aldehyde, I usually get incomplete reaction or just a trace of product. I've tried adding HMPA, but that didn't help much.

[challakrishna76]

wittig ylides( some of the higher ylides )  solubilty in single solvent  (THF ) will be less . try this mixture ( DMSO : THF = 1:1 ) and the use the base sodium hydride (with NaH = dimsyl anion formation ) and this solves u r problem of solubity and completion of the reaction and it has worked for me for one of my project

challakrishna76@gmail.com